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    首页 分子通 按分子结构分类 有机化合物 有机杂环化合物 内酯类

    内酯类

    内酯类化合物是一类含有环状结构的化合物，通常通过一个碳氧双键将两个羟基连接在一个四元、五元或六元的内环中形成。这类化合物广泛存在于自然界中，并且在有机化学、化学化工以及生物医药领域有着重要的应用价值。

    内酯的分类
    1. 按环大小划分：根据内酯环的大小，可以将其分为四元、五元和六元内酯。
    2. 按碳原子数划分：依据组成内酯的碳原子数量不同，可进一步划分为二、三、四等碳链长度不同的内酯。
    结构特征
    • 内酯结构中通常包含一个或多个环状氧基团。其独特的环状结构使得它们在水溶液中能够以开环形式存在。
    • 在生物体内，某些内酯通过酶的催化作用可实现快速转化，在药物设计和研究领域具有重要应用价值。
    应用
    1. 医药领域：许多抗生素、抗真菌药及抗癌药物都含有内酯结构。例如，四环素类抗生素就含有五元或六元内酯。
    2. 工业化学：内酯作为重要的化工原料，在合成树脂、塑料和涂料等领域有着广泛应用。
    3. 分析化学与生物传感器：利用内酯的可逆开环性质进行分析检测；通过构建特定识别分子对提高生物传感系统的特异性。
    生物活性
    • 内酯化合物通常具有一定的药理活性，如抗炎、抗菌等作用。这与其独特的空间构象和极性有关。
    • 在细胞信号传导过程中，内酯的环开裂或闭合可以影响特定蛋白质之间的相互作用。

    总之，内酯作为一种重要的化学结构单元，在多个领域发挥着不可替代的作用。

    中文名称 英文名称 CAS号 化学式 结构式图片
    —— 3-[(E)-1-hydroxybut-2-enyl]-tetrahydro-2H-pyran-2-one 1346518-36-2 C9H14O3
    3-[(E)-1-hydroxybut-2-enyl]-tetrahydro-2H-pyran-2-one
    —— (3aR,4S,6aS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one 143572-25-2 C24H28O3Si
    (3aR,4S,6aS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one
    —— (Z)-(1S,8R,9R)-8-Methyl-4-((E)-propenyl)-6,12-dioxa-tricyclo[6.2.2.0<sup>1,9</sup>]dodec-3-ene-2,5,11-trione 60958-79-4 C14H14O5
    (Z)-(1S,8R,9R)-8-Methyl-4-((E)-propenyl)-6,12-dioxa-tricyclo[6.2.2.0<sup>1,9</sup>]dodec-3-ene-2,5,11-trione
    —— 3-Fluoro-5-(iodomethyl)oxolan-2-one 129731-39-1 C5H6FIO2
    3-Fluoro-5-(iodomethyl)oxolan-2-one
    —— γ-butyrolactone-2,2-d2 531514-50-8 C4H6O2
    γ-butyrolactone-2,2-d2
    —— (3aR,4R,5R,6aS)-4-bromo-5-hydroxyhexahydro-1H-cyclopenta[c]furan-1-one 1361318-21-9 C7H9BrO3
    (3aR,4R,5R,6aS)-4-bromo-5-hydroxyhexahydro-1H-cyclopenta[c]furan-1-one
    —— 66687-62-5 C19H20O2
    —— trans-2,3-Dideutero-β-propiolacton 66263-59-0 C3H4O2
    trans-2,3-Dideutero-β-propiolacton
    —— 933451-21-9 C8H14O4
    —— 6,8-Dimethyl-oxocane-2,4-dione 129199-63-9 C9H14O3
    6,8-Dimethyl-oxocane-2,4-dione
    —— (4AS,7R,7AS)-7-Methyl-3-oxooctahydrocyclopenta[C]pyran-1-YL acetate 134906-69-7 C11H16O4
    (4AS,7R,7AS)-7-Methyl-3-oxooctahydrocyclopenta[C]pyran-1-YL acetate
    —— (3aS,5S,9aS,10S,13aR,13bS)-5-hydroxy-6,9a,14,14-tetramethyl-10-((triethylsilyl)oxy)-4,5,9a,10,11,12,13a,13b-octahydro-8H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxole-2,8,13(9H)-trione 153145-58-5 C26H40O7Si
    (3aS,5S,9aS,10S,13aR,13bS)-5-hydroxy-6,9a,14,14-tetramethyl-10-((triethylsilyl)oxy)-4,5,9a,10,11,12,13a,13b-octahydro-8H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d][1,3]dioxole-2,8,13(9H)-trione
    —— 2-Trimethylsilanyl-4-oxa-tricyclo[4.1.0.0<sup>2,7</sup>]heptane-3,5-dione 84820-07-5 C9H12O3Si
    2-Trimethylsilanyl-4-oxa-tricyclo[4.1.0.0<sup>2,7</sup>]heptane-3,5-dione
    —— 2-(2-Hydroxypropyl)-γ-valerolacton 2957-64-4 C8H14O3
    2-(2-Hydroxypropyl)-γ-valerolacton
    —— methyl 5,5-dimethyl-3-oxo-2a,3,5a,6-tetrahydro-5H-furo-<3,4-c>-pyrazole-2a-carboxylate 76139-23-6 C9H12N2O4
    methyl 5,5-dimethyl-3-oxo-2a,3,5a,6-tetrahydro-5H-furo-<3,4-c>-pyrazole-2a-carboxylate
    —— rel-(3aR,4R,7aS)-6-(t-butyldimethylsilyloxymethyl)-4-hydroxy-3a,4,7,7a-tetrahydrobenzofuran-2(3H)-one 92463-83-7 C15H26O4Si
    rel-(3aR,4R,7aS)-6-(t-butyldimethylsilyloxymethyl)-4-hydroxy-3a,4,7,7a-tetrahydrobenzofuran-2(3H)-one
    —— (2R,3S)-3-[(2S)-butan-2-yl]-4-oxooxetane-2-carbaldehyde 933451-22-0 C8H12O3
    (2R,3S)-3-[(2S)-butan-2-yl]-4-oxooxetane-2-carbaldehyde
    —— (3aR,4S,7aS)-2-Oxo-2,3,3a,4,5,7a-hexahydro-benzofuran-4-carboxylic acid methyl ester 71367-26-5 C10H12O4
    (3aR,4S,7aS)-2-Oxo-2,3,3a,4,5,7a-hexahydro-benzofuran-4-carboxylic acid methyl ester
    —— 1192231-14-3 C10H18O4
    —— (1S,4S,5S)-4-Hydroxy-6-oxa-bicyclo[3.2.2]nonan-7-one 84033-88-5 C8H12O3
    (1S,4S,5S)-4-Hydroxy-6-oxa-bicyclo[3.2.2]nonan-7-one
    —— 81723-13-9 C21H28O2
    —— (3R,5S,6S)-5-Methoxy-6-((1S,3R)-1-methoxy-3-methyl-5-oxo-hexyl)-3-methyl-tetrahydro-pyran-2-one 135912-32-2 C15H26O5
    (3R,5S,6S)-5-Methoxy-6-((1S,3R)-1-methoxy-3-methyl-5-oxo-hexyl)-3-methyl-tetrahydro-pyran-2-one
    —— (R)-6-Hydroxy-5-methyl-3,4,5,5a,6,7,8,8a-octahydro-naphtho[1,8-bc]furan-2-one 66278-38-4 C12H16O3
    (R)-6-Hydroxy-5-methyl-3,4,5,5a,6,7,8,8a-octahydro-naphtho[1,8-bc]furan-2-one
    —— 2-oxa-spiro[4.5]deca-6,9-diene-1,8-dione 19672-84-5 C9H8O3
    2-oxa-spiro[4.5]deca-6,9-diene-1,8-dione
    —— bromo-[2-(2-methyl-5-oxooxolan-2-yl)ethyl]mercury 87433-86-1 C7H11BrHgO2
    bromo-[2-(2-methyl-5-oxooxolan-2-yl)ethyl]mercury
    —— 2,2'-Dimethyl-5,5'-dioxo-octahydro-[2,2']bifuranyl-4,4'-dicarboxylic acid 65461-15-6 C12H14O8
    2,2'-Dimethyl-5,5'-dioxo-octahydro-[2,2']bifuranyl-4,4'-dicarboxylic acid
    —— 3β,18-dihydroxy-5β-androstane-17β-carboxylic acid lactone 86698-74-0 C20H30O3
    3β,18-dihydroxy-5β-androstane-17β-carboxylic acid lactone
    —— simplexolide A 1346231-38-6 C17H30O3
    simplexolide A
    —— (3S,4S,5S,6R)-4-hydroxy-6-((S)-1-hydroxypropan-2-yl)-3,5-dimethyltetrahydro-2H-pyran-2-one 1096707-32-2 C10H18O4
    (3S,4S,5S,6R)-4-hydroxy-6-((S)-1-hydroxypropan-2-yl)-3,5-dimethyltetrahydro-2H-pyran-2-one
    —— 4-Methyl-8-phenyl-1-oxa-spiro[4.5]decan-2-one 74603-50-2 C16H20O2
    4-Methyl-8-phenyl-1-oxa-spiro[4.5]decan-2-one
    —— α,γ-diphenyl<γ-13C>butyrolactone 94848-88-1 C16H14O2
    α,γ-diphenyl<γ-13C>butyrolactone
    —— (3R,4S,5S,6R)-4-hydroxy-6-((S)-1-hydroxypropan-2-yl)-3,5-dimethyltetrahydro-2H-pyran-2-one 1096707-31-1 C10H18O4
    (3R,4S,5S,6R)-4-hydroxy-6-((S)-1-hydroxypropan-2-yl)-3,5-dimethyltetrahydro-2H-pyran-2-one
    —— (4R<sup>*</sup>,5S<sup>*</sup>)-4-ethyl-4-hydroxy-5-methyl-1-oxacycloheptan-2-one 135974-28-6 C9H16O3
    (4R<sup>*</sup>,5S<sup>*</sup>)-4-ethyl-4-hydroxy-5-methyl-1-oxacycloheptan-2-one
    —— (1S,5S,6R)-6-(Triethylsilyloxy)-2-oxabicyclo<3.2.1>octan-3-one 128039-83-8 C13H24O3Si
    (1S,5S,6R)-6-(Triethylsilyloxy)-2-oxabicyclo<3.2.1>octan-3-one
    —— (+)-(5R)-dihydro-5-(3'-hydroxypropyl)-2(3H)-furanone 98611-85-9 C7H12O3
    (+)-(5R)-dihydro-5-(3'-hydroxypropyl)-2(3H)-furanone
    —— 2,2-Dibutyl-8-(3-hydroxy-phenyl)-1,3-dioxa-7,9-dithia-2-stanna-cyclododecane-4,12-dione 89305-03-3 C21H32O5S2Sn
    2,2-Dibutyl-8-(3-hydroxy-phenyl)-1,3-dioxa-7,9-dithia-2-stanna-cyclododecane-4,12-dione
    —— 6(R)-[2-[8(S)-(2,2-Dimethylbutyryloxy)-2(S)-methyl-6(S)-carboxy-1,2,3,4,4a(S),5,6,7,8,8a(S)-decahydronaphthyl-1(S)]ethyl]-4(R)-(tert-butyldimethylsilyloxy) 3,4,5,6-tetrahydro-2H-pyran-2-one 114801-77-3 C31H54O7Si
    6(R)-[2-[8(S)-(2,2-Dimethylbutyryloxy)-2(S)-methyl-6(S)-carboxy-1,2,3,4,4a(S),5,6,7,8,8a(S)-decahydronaphthyl-1(S)]ethyl]-4(R)-(tert-butyldimethylsilyloxy) 3,4,5,6-tetrahydro-2H-pyran-2-one
    —— γ-(1-ethoxyvinyl)-γ-butyrolactone 147721-39-9 C8H12O3
    γ-(1-ethoxyvinyl)-γ-butyrolactone
    —— 3-benzyl-6-phenyldihydro-2H-pyran-2,4(3H)-dione 1020850-93-4 C18H16O3
    3-benzyl-6-phenyldihydro-2H-pyran-2,4(3H)-dione
    —— 3,6-Dimethyl-10-oxa-tricyclo[4.4.0.0<sup>2,8</sup>]dec-3-en-9-one 129666-98-4 C11H14O2
    3,6-Dimethyl-10-oxa-tricyclo[4.4.0.0<sup>2,8</sup>]dec-3-en-9-one
    —— (R)-dihydro-5-((R)-1-hydroxybut-3-enyl)furan-2(3H)-one 213414-10-9 C8H12O3
    (R)-dihydro-5-((R)-1-hydroxybut-3-enyl)furan-2(3H)-one
    —— 83997-34-6 C14H20O3
    —— 3-(2-hydroxy-propyl)-3,5-dimethyl-dihydro-furan-2-one 65668-66-8 C9H16O3
    3-(2-hydroxy-propyl)-3,5-dimethyl-dihydro-furan-2-one
    —— 3-[5-(ethoxymethyl)-2-oxotetrahydrofuran-3-yl]propionic acid 1338212-46-6 C10H16O5
    3-[5-(ethoxymethyl)-2-oxotetrahydrofuran-3-yl]propionic acid
    —— 3-(Oxiran-2-ylmethyl)-oxolan-2-one 1351932-55-2 C7H10O3
    3-(Oxiran-2-ylmethyl)-oxolan-2-one
    —— 4,6,6-Trimethyl-3a,6,7,7a-tetrahydro-3H-benzofuran-2-one 124938-37-0 C11H16O2
    4,6,6-Trimethyl-3a,6,7,7a-tetrahydro-3H-benzofuran-2-one
    —— [(4aS,5S,6S,8S,8aS)-5-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-3-oxo-8a-vinyl-octahydro-isochromen-6-yl]-acetic acid methyl ester 69225-47-4 C20H34O6Si
    [(4aS,5S,6S,8S,8aS)-5-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-3-oxo-8a-vinyl-octahydro-isochromen-6-yl]-acetic acid methyl ester
    —— methyl 3-hydroxy-4-methyl-5(2H)-oxo-2-tridecyl-dihydrofuran-3-carboxylate 1258168-27-2 C20H36O5
    methyl 3-hydroxy-4-methyl-5(2H)-oxo-2-tridecyl-dihydrofuran-3-carboxylate
    —— (Z)-4,4-Dimethyl-7-phenyl-2-oxo-6-hydroximino-2H,4H,5H,6H,7H-furo-<3,4-b>pyran 72900-54-0 C15H15NO4
    (Z)-4,4-Dimethyl-7-phenyl-2-oxo-6-hydroximino-2H,4H,5H,6H,7H-furo-<3,4-b>pyran
    —— (1S,5S)-5-Trimethylsilanylethynyl-6-oxa-bicyclo[3.2.1]oct-2-en-7-one 134224-27-4 C12H16O2Si
    (1S,5S)-5-Trimethylsilanylethynyl-6-oxa-bicyclo[3.2.1]oct-2-en-7-one